Historic Route 66 Kid friendly Vacations
Book a Kid friendly Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Kid friendly vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was ￥126,644, price is now ￥85,894 per person
￥85,894
per person
Mar 13 - Mar 18
found 5 hours ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic.
Reviewed on Jan 20, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥206,913, price is now ￥118,750 per person
￥118,750
per person
Mar 13 - Mar 18
found 5 hours ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Superb customer service and staff, clean room and common areas, and awesome breakfast buffet.
Reviewed on Jan 27, 2026
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was ￥185,520, price is now ￥119,804 per person
￥119,804
per person
Mar 13 - Mar 18
found 5 hours ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
9/10 Wonderful! (766 reviews)
Great stay. Would come again.
Reviewed on Jan 19, 2026
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was ￥177,666, price is now ￥115,384 per person
￥115,384
per person
Mar 13 - Mar 18
found 5 hours ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again.
Reviewed on Jan 25, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥171,219, price is now ￥116,543 per person
￥116,543
per person
Mar 13 - Mar 18
found 5 hours ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Clean room and amenities
Reviewed on Jan 8, 2026
Don't see what you're looking for?
See all available trips from Wilkes-Barre to Historic Route 66
View all trips5* Kid friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥360,070, price is now ￥301,847 per person
￥301,847
per person
Mar 11 - Mar 14
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥385,894, price is now ￥339,514 per person
￥339,514
per person
Mar 11 - Mar 14
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The best hotel ! Always pleasant to stay !
Reviewed on Jan 27, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Historic Route 66
View all trips3 Night Kid friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥316,616, price is now ￥269,518 per person
￥269,518
per person
Mar 11 - Mar 14
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Superb customer service and staff, clean room and common areas, and awesome breakfast buffet.
Reviewed on Jan 27, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥360,070, price is now ￥301,847 per person
￥301,847
per person
Mar 11 - Mar 14
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥385,894, price is now ￥339,514 per person
￥339,514
per person
Mar 11 - Mar 14
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The best hotel ! Always pleasant to stay !
Reviewed on Jan 27, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Historic Route 66
View all trips4 Night Kid friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥154,750, price is now ￥103,774 per person
￥103,774
per person
Mar 18 - Mar 22
found 5 hours ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Superb customer service and staff, clean room and common areas, and awesome breakfast buffet.
Reviewed on Jan 27, 2026
The Emily Hotel
Downtown Chicago
Price was ￥160,912, price is now ￥115,560 per person
￥115,560
per person
Mar 18 - Mar 22
found 5 hours ago
Roundtrip flight included
Wilkes-Barre (AVP) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again.
Reviewed on Jan 25, 2026
Don't see what you're looking for?
See all available trips from Wilkes-Barre to Historic Route 66
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
